Sodium Carbonate → 4-((1R,4R,5S,8S,12R)-4-methyl-2,6-dioxo-9,13-dioxa-7-azatetracyclo[6.3.1.11,4.05,12]tridec-7-yl)-2-(trifluoromethyl)benzonitrile

HRID 563902Notes

Reaction equation

HRID 563902 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[OH:23][C@H:24]1[CH2:34][C@@:33]2([CH3:36])[O:35][C@@:25]31[C@@H:37]1[C@@H:29]([N:30]([C:39]4[CH:46]=[CH:45][C:42]([C:43]#[N:44])=[C:41]([C:47]([F:50])([F:49])[F:48])[CH:40]=4)[C:31](=[O:38])[C@H:32]21)[O:28][CH2:27][CH2:26]3.[O-]S([O-])(=S)=O.[Na+].[Na+].C([O-])([O-])=O.[Na+].[Na+]>C1COCC1.C(Cl)Cl>[CH3:36][C@:33]12[O:35][C@:25]3([C@@H:37]4[C@@H:29]([N:30]([C:39]5[CH:46]=[CH:45][C:42]([C:43]#[N:44])=[C:41]([C:47]([F:49])([F:50])[F:48])[CH:40]=5)[C:31](=[O:38])[C@H:32]14)[O:28][CH2:27][CH2:26]3)[C:24](=[O:23])[CH2:34]2

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 59635881Benzonitrile, 4-((3aR,4S,6R,6aS,8aS,8bR)-octahydro-4-hydroxy-6-methyl-7-oxo-3a,6-epoxy-3ah-pyrano(2,3,4-cd)isoindol-8(4H)-yl)-2-(trifluoromethyl)-

Product 1

HCID 596360594-((1R,4R,5S,8S,12R)-4-methyl-2,6-dioxo-9,13-dioxa-7-azatetracyclo[6.3.1.11,4.05,12]tridec-7-yl)-2-(trifluoromethyl)benzonitrileYield 97.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

Dess-Martin periodinane (12 g, 28.3 mmol) was added to a solution of Example 3 (3.0 g, 7.6 mmol) in THF (20 mL) and CH2Cl2 (30 mL) at room temperature. The reaction mixture was stirred at room temperature for 18 h and CH2Cl2 (50 mL), aq. 15% Na2S2O3 solution (25 mL), and aq. 2M Na2CO3 solution (25 mL) were added. The mixture was stirred for 1 h and the layers were separated. The organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure to give 2.9 g (97%) of the Example 5.

Workup

  1. stirringThe mixture was stirred for 1 h
  2. customthe layers were separated
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8a46be3b7eed478d9ea60b876fa52b5a
Source dataset
uspto-grants-2011_11
Patent number
US08067582B2

Reaction notes

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